FAD’s Hot Picks for Fall Festivals & Apple Picking In and Around Fairfield County

September 14–20, 2026 Fall entertainment is kicking into high gear, and Fairfield After Dark has your week covered! From comedy and live music to vineyard happenings, a legendary cultural commentator and artisan shopping, there are plenty of reasons to get out this week. Here are FAD’s Top Picks for September 14–20! 🍷 TUESDAY, SEPTEMBER 15 | AQUILA’S NEST VINEYARDS — NEWTOWN Kick off the week at Aquila’s Nest Vineyards with Whispers From Heaven with Patricia Griffin . Enjoy the vineyard setting while checking out one of the many special experiences happening throughout the week. 👉 GET THE DETAILS & PLAN YOUR VISIT HERE 😂 WEDNESDAY, SEPTEMBER 16 | NEW YORK COMEDY CLUB — STAMFORD Need a midweek laugh? Mike Cannon hits the stage at New York Comedy Club Stamford Wednesday at 7 PM . 👉 GRAB YOUR TICKETS HERE 🍷 WEDNESDAY, SEPTEMBER 16 | AQUILA’S NEST VINEYARDS — NEWTOWN Put on those boots and head to Newtown! Country Line Dancing is on the schedule Wednesday at Aquila’s Nest Vineyards. 👉 GET THE DETAILS HERE 💕 WEDNESDAY, SEPTEMBER 16 | ODEEN’S at Oak Hills - Norwalk Meet local singles ages 25–39 face-to-face at ODEEN’S Oak Hills for a fun, low-pressure evening of speed dating, guided conversations, and the chance to make a real connection. 👉 Tickets are limited GRAB YOUR TICKETS HERE 🎹 THURSDAY, SEPTEMBER 17 | THE BILLY JOEL LEGACY — THE PALACE STAMFORD The music of the Piano Man comes alive when The Billy Joel Legacy: A Tribute Experience takes the stage at The Palace Stamford Thursday at 7:30 PM . Billy Joel fans, this one's for you! 👉 GRAB YOUR TICKETS HERE 🍷 THURSDAY, SEPTEMBER 17 | AQUILA’S NEST VINEYARDS — NEWTOWN Aquila’s Nest keeps the week going with several Thursday experiences, including Pilates, Plant Bingo and special workshops . 👉 GET THE DETAILS HERE 🎤 FRIDAY, SEPTEMBER 18 | FRAN LEBOWITZ — EDMOND TOWN HALL, NEWTOWN Known for her razor-sharp wit, unapologetic opinions and hilarious observations on modern life, Fran Lebowitz comes to Edmond Town Hall Friday at 8 PM . Doors open at 7 PM. 👉 GRAB YOUR TICKETS HERE 🎤 FRIDAY, SEPTEMBER 18 | SIMPLY THE BEST — THE PALACE STAMFORD Get ready for the music of Tina Turner! Simply The Best: A Tribute to the Music of Tina Turner takes over The Palace Stamford Friday at 8 PM . 👉 GRAB YOUR TICKETS HERE 😂 FRIDAY, SEPTEMBER 18 | CAITLIN PELUFFO — NEW YORK COMEDY CLUB STAMFORD Start your weekend laughing with Caitlin Peluffo , performing two shows Friday night at 7 PM and 9:30 PM . 👉 GRAB YOUR TICKETS HERE 🦙🍷 FRIDAY, SEPTEMBER 18 | AQUILA’S NEST VINEYARDS — NEWTOWN Friday brings even more fun to Aquila’s Nest with Llamas & Llibations and Cruise Night . 👉 GET THE DETAILS HERE 🛍️ SATURDAY, SEPTEMBER 19 | POP SHOP MARKET — DARIEN COMMONS Shop small and discover something different when PopShop Market returns to Darien Commons Saturday from 11 AM–5 PM . Explore a curated collection of independent makers and small businesses offering apparel, jewelry, home décor, self-care products, gifts and plenty of one-of-a-kind finds. 👉 GET ALL THE DETAILS HERE 😂 SATURDAY, SEPTEMBER 19 | NEW YORK COMEDY CLUB — STAMFORD Saturday starts early with Early Bird Comedy at 4:30 PM , followed by another performance from Caitlin Peluffo at 7 PM . 👉 GRAB YOUR TICKETS HERE 🍷🎸 SATURDAY, SEPTEMBER 19 | THE 80s ROCK EXPERIENCE — AQUILA’S NEST VINEYARDS Turn back the clock at Aquila’s Nest with The 80s Rock Experience Tribute Show , happening Saturday from 6–9 PM . 👉 GRAB YOUR TICKETS & GET THE DETAILS HERE 🎹 SATURDAY, SEPTEMBER 19 | THE MIGHTY FRANKLIN BROTHERS — THE PALACE DANBURY Steely Dan fans, this one's for you! The Mighty Franklin Brothers take over The Palace Danbury Saturday at 7:30 PM . Led by brothers Jay and Carl Franklin and backed by a powerhouse lineup of musicians and horns, the band brings the sophisticated arrangements, soulful vocals and unmistakable sound of Steely Dan to the stage. 👉 GRAB YOUR TICKETS HERE 🎬🎶 SATURDAY, SEPTEMBER 19 | LABYRINTH IN CONCERT — THE PALACE STAMFORD Celebrate 40 years of a cult classic with Jim Henson’s Labyrinth: In Concert — 40th Anniversary at The Palace Stamford Saturday at 7:30 PM. 👉 GRAB YOUR TICKETS HERE 🎶 SUNDAY, SEPTEMBER 20 | GREEN EYED LADY — ODEEN’S OAK HILLS, NORWALK Wrap up the weekend with dinner and live music! Green Eyed Lady performs at Odeen’s Oak Hills Sunday from 4–7 PM . 👉 Make a Reservation here! ⭐ GET OUT & HAVE SOME FUN! From Newtown to Stamford, Darien, Danbury, Ridgefield, New Canaan and Norwalk , there’s plenty happening this week. These are just a few of FAD’s Top Picks — grab your tickets, make those reservations and start planning your week early! 🎶 😂 🍷 🛍️ 🎭 Get Out. Have Fun. Live Local. See even more concerts, comedy, festivals, fairs, fall happenings and Things To Do in and around Fairfield County at FairfieldAfterDark.com.

Milford, CT: Downtown Milford will come alive with the sounds of jazz on Saturday, October 3, 2026 , as the Milford Arts Council presents the inaugural Jazz’n Downtown , a new immersive celebration combining live music, local art, dining and the charm of one of Connecticut’s favorite shoreline downtowns. Presented with lead Presenting Sponsor Coastal Bridge Advisors , Jazz’n Downtown is designed to be explored at your own pace. Visitors can arrive by train, car, boat, bike or foot and spend the day strolling Milford’s historic neighborhoods, waterways, boutiques, restaurants and artisan displays — all while live jazz provides the soundtrack. Jazz Throughout Downtown Milford Award-winning jazz performers will take the stage at three outdoor venues , including locations along Milford’s scenic waterfront. The music continues throughout the downtown experience, with solo and duo jazz performers appearing at participating restaurants during brunch, lunch and dinner. It’s more than a traditional music festival. Jazz’n Downtown brings music, art, food and community together throughout the heart of Milford, allowing guests to create their own experience and discover something new around every corner. An Evening Celebrating Ella & Louis The celebration continues that evening at Parsons Veterans’ Memorial Hall with a special tribute concert honoring two of jazz music’s most legendary performers, Ella Fitzgerald and Louis Armstrong . The evening concert requires a separate ticket, while VIP packages offer an enhanced Jazz’n Downtown experience with reserved seating areas, an early reservation window for brunch, lunch and dinner, parking and reserved seating for the evening concert. About the Milford Arts Council Founded in 1972, the Milford Arts Council (MAC) is a nonprofit organization dedicated to connecting and enriching the community through music, theater, visual arts, dance, film and creative expression. MAC presents more than 200 events annually and operates from the beautifully restored historic eastbound Milford train station, as well as the Firehouse Gallery at Walnut Beach. Jazz’n Downtown 📅 Saturday, October 3, 2026 📍 Downtown Milford, Connecticut 🎷 Event Information: jazzndowntown.org 🎟️ Tickets: Eventbrite – Jazz’n Downtown: The Ultimate Jazz & Arts Experience 🎨 Milford Arts Council: milfordarts.org ☎️ Information: 203-878-6647 Come for the jazz, explore downtown Milford, discover local artists, enjoy great food and make a full day — and night — of this brand-new Connecticut arts experience.

Stamford, CT: Early Bird pricing ends Sept. 15 at 11:59 PM for WineFest on Bedford, happening Oct. 3 at Latham Park in Stamford Downtown.

There’s something about fall in Connecticut that just makes you want to grab a sweater, jump in the car and head to a farm. Pumpkin patches are opening, cider donuts are calling, corn mazes are ready to be conquered, and our Fairfield County countryside is about to put on its annual show of spectacular fall color. Whether you're searching for the perfect pumpkin to carve, planning a family outing with the kids, looking for a fall date-day destination or simply want an excuse to get outside and enjoy autumn, Fairfield After Dark has rounded up some of our favorite pumpkin-picking destinations in and around Fairfield County. And we’re not stopping at the county line! We’ve included farms in neighboring New Haven and Litchfield Counties, plus some great destinations just across the New York border in Westchester, Putnam and nearby Dutchess County. FAIRFIELD COUNTY PUMPKIN PATCHES BETHEL Blue Jay Orchards - 125 Plumtrees Road, Bethel A Fairfield County fall classic! Blue Jay Orchards combines its beautiful orchard setting with a seasonal pumpkin patch, farm market and bakery. The 2026 pumpkin patch opened September 12 with pumpkins ranging from decorative minis and specialty varieties to jumbo jack-o'-lantern candidates. Be sure to make time for cider and those famous cider donuts before heading home. EASTON Silverman's Farm - 451 Sport Hill Road, Easton Silverman’s has been part of the Easton landscape for generations and remains one of Fairfield County’s quintessential fall destinations. Stop for pumpkins and fall decorations, visit the country market for pies, cider and seasonal goodies, and make some time for the farm’s popular Animal Farm. NEWTOWN Castle Hill Farm - Sugar Lane, Newtown If you want the full pumpkin-picking experience, Castle Hill deserves a spot on your fall bucket list. The family farm features a four-acre pick-your-own pumpkin patch with dozens of varieties of pumpkins, gourds and squash, along with its popular corn maze and hayrides. It’s one of those places where pumpkin picking can easily turn into an entire fall afternoon. REDDING Warrup’s Farm - 11 John Read Road, Redding For those who prefer a smaller, old-fashioned farm experience, Warrup’s is a wonderful Redding tradition. The working family farm has long been associated with seasonal produce and fall pumpkin activities and offers a decidedly more rustic alternative to some of the larger fall attractions. SHELTON Pumpkinseed Hill Farm of Jones Family Farms 120 Beardsley Road, Shelton One of the biggest names in Connecticut pumpkin picking, Jones Family Farms turns Pumpkinseed Hill into a fall destination each year. Search the fields for pumpkins in all shapes, colors and sizes, explore the farm, tackle the mini corn maze and add a tractor-drawn hayride to your visit. Reservations are encouraged for the Pumpkinseed Hill Exploration, particularly on busy weekends. Wells Hollow Farms - 656 Bridgeport Avenue, Shelton Another Shelton option for families looking to make an afternoon of it. Wells Hollow offers a festive farm atmosphere with pumpkins, seasonal decorations, a corn maze, animals and plenty of opportunities to enjoy a classic New England fall day. STAMFORD St. John's Luthern Church – 884 Newfield Avenue, Stamford The St. John’s Lutheran Church Pumpkin Patch is an annual October tradition and mission fundraiser featuring hundreds of pumpkins for sale throughout the month. Best of all, proceeds from every pumpkin sold are donated to support those in need. TRUMBULL Plasko's Farm Creamery & Cafe - 670 Daniels Farm Road, Trumbull A longtime Trumbull farm and a fun stop during fall. Plasko’s combines its farm setting with a bakery, café and homemade ice cream, making it an easy addition to a Fairfield County fall drive — especially when cider donuts and ice cream are part of the plan. JUST OVER THE FAIRFIELD COUNTY LINE Some of Connecticut's best pumpkin-picking destinations are only a short drive beyond Fairfield County. These New Haven and Litchfield County farms are particularly convenient for residents of northern and eastern Fairfield County. NEW HAVEN COUNTY BETHANY Clover Nook Farm - 50 Fairwood Road, Bethany This historic family farm dates back generations and offers a traditional farm-market experience. During fall, pumpkins join the farm’s lineup of seasonal produce, flowers, corn stalks, mums and other harvest favorites. Connecticut tourism resources also identify Clover Nook as a pick-your-own pumpkin destination. ORANGE Treat Farm 361 Old Tavern Road, Orange Treat Farm is a great choice for families who like a less commercial farm experience. In addition to seasonal farm offerings, its corn maze has become a fall attraction of its own. It’s an easy trip from lower Fairfield County and the Valley. OXFORD Belinsky Farm - 124 Moose Hill Road, Oxford Right above the Fairfield County line, Belinsky Farm is a terrific option for residents of Shelton, Monroe and Newtown. This smaller family farm offers an old-school farm atmosphere with seasonal pick-your-own crops and fall favorites including pumpkins, gourds and squash. LITCHFIELD COUNTY — WORTH THE SHORT DRIVE NORTH BETHLEHEM March Farm - 160 Munger Lane, Bethlehem This one deserves a fall road trip. March Farm's Hilltop offers beautiful Litchfield County views along with pick-your-own apples and pumpkins, a corn maze, hayrides, food and seasonal activities. Pick-your-own pumpkins generally begins in late September or early October and continues through October. Weekend visits can also include rotating food vendors and live music. WOODBURY Logue Farms, Inc. - Woodbury Looking for a classic country pumpkin-picking experience? Logue Farms is known for its seasonal pumpkin patch and hayride experience. It’s a particularly convenient Litchfield County destination from Southbury, Newtown and northern Fairfield County. LITCHFIELD Bunnell Farm - 498 Maple Street, Litchfield Make a fall foliage drive out of this one. Bunnell Farm's pumpkin season is typically centered around weekends and combines a traditional farm setting with some beautiful Litchfield County scenery. Fox and the Buck Farm, Inc. - 280 Northfield Road, Litchfield If unusual pumpkins are more your style, put Fox and the Buck on your radar. The seasonal family farm specializes in flowers and heirloom pumpkins — perfect for anyone searching for something a little different for the front porch. PUMPKIN PICKING JUST ACROSS THE NEW YORK BORDER Fairfield County residents shouldn't forget about our neighbors to the west. Northern Westchester and Putnam County are practically an extension of our fall playground, and several farms are an easy drive from Greenwich, Stamford, New Canaan, Ridgefield, Danbury and surrounding towns. NORTH SALEM, WESTCHESTER COUNTY Outhouse Orchards - 139 Hardscrabble Road, North Salem If you're looking for a full-scale fall festival, this is one to know. Outhouse Orchards' 2026 Fall Festival runs from August 30 through November 1 and includes a pumpkin patch, apple picking, corn maze, hayrides, photo opportunities, family attractions, farm market, food and seasonal treats. Admission is ticketed during the festival, so check ahead before heading across the border. Harvest Moon Farm & Orchard - 130 Hardscrabble Road, North Salem Practically next door to Outhouse Orchards, Harvest Moon is another popular Westchester fall destination. Expect the combination of orchard scenery, seasonal pumpkin experiences, family activities, food, cider and plenty of fall photo opportunities. GRANITE SPRINGS / SOMERS, WESTCHESTER COUNTY Stuarts Farm - 62 Granite Springs Road, Granite Springs If the giant fall-festival atmosphere isn't your thing, Stuart's is worth considering. This longtime family farm offers a more traditional Hudson Valley orchard experience with seasonal pumpkin picking, apples, a farm stand, bakery treats and a relaxed country setting. BREWSTER, PUTNAM COUNTY Salinger's Orchard - 230 Guinea Road, Brewster Salinger's is an easy ride from the Danbury and Ridgefield areas and a great stop for anyone who loves the farm-market side of fall. The longtime family orchard is especially known for its bakery, pies, cider donuts and seasonal produce. Think of this one more as a fall farm-market destination than a major pick-your-own pumpkin attraction. PAWLING, DUTCHESS COUNTY Dykeman Farm - 31 Dykeman Lane, Pawling Just beyond Putnam County, Dykeman Farm is worth adding to the list for northern Fairfield County residents. The fourth-generation family farm is known for a genuine pick-your-own pumpkin experience with a huge variety of pumpkins and a refreshingly traditional farm atmosphere. 🎃 MAKE A DAY OF IT! One of the best things about living in Fairfield County is that you don't have to travel very far to experience a picture-perfect New England fall. Start close to home in Bethel, Easton, Newtown, Redding, Shelton, Westport, Ridgefield or Trumbull — or turn pumpkin picking into a fall road trip through the rolling hills of Litchfield County or across the border into Westchester and the Hudson Valley. Pack the kids. Grab the camera. Bring home a pumpkin — or five. And whatever you do, don't forget the cider donuts! FAD TIP: Pumpkin availability, hayrides, corn mazes and special activities can change because of weather and crop conditions. Always check directly with the farm before heading out, particularly later in October. Happy Pumpkin Picking from Fairfield After Dark! 🎃🍎🍂 

Love shopping small and discovering something you won’t find everywhere else? PopShop Market is bringing its popular curated artisan markets to Fairfield, Darien, Westport and Milford throughout the rest of 2026. PopShop isn’t your typical vendor fair. Each market features a carefully curated, hand-picked selection of artisans, makers, designers, boutiques and small businesses , offering everything from clothing and jewelry to home décor, specialty goods, self-care products and unique gifts. 🛍️ Save the Dates! DARIEN — Darien Commons 📅 September 19 • October 17 • November 21 FAIRFIELD — Elicit Brewing Co. 📅 September 27 • November 22 • December 6 WESTPORT — Westport Museum for History & Culture 📅 October 3 • November 15 MILFORD — Historic Milford Green 📅 November 7 With the holiday season approaching, PopShop is a great place to shop small, support local and find one-of-a-kind gifts while meeting some of the talented people behind the products. The best part? Every PopShop is different. The vendor lineup changes from market to market, so there’s always something new to discover. Grab a friend, make a day of it and see what catches your eye! SHOP SMALL 💛 SUPPORT LOCAL 💛 DISCOVER THE UNIQUE!